title: Production of novel antioxidative prenyl naphthalen-ols by combinational bioconversion with dioxygenase PhnA1A2A3A4 and prenyltransferase NphB or SCO7190.
abstract: We performed combinational bioconversion of substituted naphthalenes with PhnA1A2A3A4 (an aromatic dihydroxylating dioxygenase from marine bacterium Cycloclasticus sp. strain A5) and prenyltransferase NphB (geranyltransferase from Streptomyces sp. strain CL190) or SCO7190 (dimethylallyltransferase from Streptomyces coelicolor A3(2)) to produce prenyl naphthalen-ols. Using 2-methylnaphthalene, 1-methoxynaphthalene, and 1-ethoxynaphthalene as the starting substrates, 10 novel prenyl naphthalen-ols were produced by combinational bioconversion. These novel prenyl naphthalen-ols each showed potent antioxidative activity against a rat brain homogenate model. 2-(2,3-Dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one (2',3'-dihydroxychrysin) generated with another aromatic dihydroxylating dioxygenase and subsequent dehydrogenase was also geranylated at the C-5'-carbon by the action of NphB.
authors.affiliation: Department of Food and Nutrition, Japan Women's University, Tokyo, Japan. kshindo@fc.jwu.ac.jp
authors.forename: Kazutoshi
authors.initials: K
authors.lastname: Shindo
authors.forename: Ayako
authors.initials: A
authors.lastname: Tachibana
authors.forename: Ayumi
authors.initials: A
authors.lastname: Tanaka
authors.forename: Shizuka
authors.initials: S
authors.lastname: Toba
authors.forename: Emi
authors.initials: E
authors.lastname: Yuki
authors.forename: Taro
authors.initials: T
authors.lastname: Ozaki
authors.forename: Takuto
authors.initials: T
authors.lastname: Kumano
authors.forename: Makoto
authors.initials: M
authors.lastname: Nishiyama
authors.forename: Norihiko
authors.initials: N
authors.lastname: Misawa
authors.forename: Tomohisa
authors.initials: T
authors.lastname: Kuzuyama
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000494:pharmacology; D001711:Biotransformation; D001921:Brain / Q000378:metabolism; D002474:Cell-Free System / Q000378:metabolism*; D003001:Cloning, Molecular; D004122:Dimethylallyltranstransferase / Q000235:genetics / Q000378:metabolism*; D049308:Dioxygenases / Q000235:genetics / Q000378:metabolism*; D004926:Escherichia coli; D015870:Gene Expression; D015227:Lipid Peroxidation / Q000187:drug effects*; D009281:Naphthalenes / Q000737:chemistry; D010084:Oxidation-Reduction / Q000187:drug effects*; D044147:Piscirickettsiaceae / Q000737:chemistry / Q000201:enzymology; D054876:Prenylation; D051381:Rats; D011994:Recombinant Proteins / Q000235:genetics / Q000378:metabolism*; D013302:Streptomyces / Q000737:chemistry / Q000201:enzymology
chemical_list: D000975:Antioxidants; D009281:Naphthalenes; D011994:Recombinant Proteins; C448759:1-methoxynaphthalene; D049308:Dioxygenases; D004122:Dimethylallyltranstransferase; C027384:2-methylnaphthalene